1-Phenylpiperazine → 1-[5-(3,4-Dimethylphenyl)-furan-2-ylmethyl]-4-phenylpiperazine

HRID 1112744Notes

Reaction equation

HRID 1112744 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[O:13][C:12]([CH:14]=O)=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].[C:16]1([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CO.Cl.C([BH3-])#N.[Na+]>CO>[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[O:13][C:12]([CH2:14][N:25]3[CH2:26][CH2:27][N:22]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH2:23][CH2:24]3)=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

6

Reactant 4

HCID 70961-PhenylpiperazineHCID 9601395-(3,4-Dimethylphenyl)furan-2-carbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 21893726Hydrochloride methanol

Product 1

HCID 227625161-[5-(3,4-Dimethylphenyl)-furan-2-ylmethyl]-4-phenylpiperazine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

5-(3,4-Dimethylphenyl)-furan-2-carboxaldehyde (4.0g;0.02 mole), prepared by the method of C. S. Davis and G. S. Lougheed J.Het.Chem. 4,153, (1967), was added rapidly to a stirred solution of N-phenylpiperazine (3.2g; 0.02 mole) in methanol (30ml) adjusted to pH 7 (using MeOH/HCl). After 30 minutes a solution of sodium cyanoborohydride (0.48g; 0.0075 mole) in methanol (10ml) was added dropwise and the mixture stirred at room temperature for 2 hours. After removal of the methanol by evaporation, the resultant solid was purified by silica gel chromatography. The fractions containing the desired compound were combined, evaporated and the crystalline solid which formed was recrystallised from 60/80° C. petroleum ether to give the title compound, m.p. 110° C.

Workup

  1. customAfter removal of the methanol
  2. customby evaporation
  3. customthe resultant solid was purified by silica gel chromatography
  4. additionThe fractions containing the desired compound
  5. customevaporated
  6. customthe crystalline solid which formed
  7. customwas recrystallised from 60/80° C. petroleum ether

Sources & evidence

ORD record
ord-10bd93d474fe453dabfd23b6c88cdfec
Source dataset
uspto-grants-1978_10
Patent number
US04123529

Reaction notes

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